TWI415626B - 標記〔f-18〕之l-麩胺酸,標記〔f-18〕之l-麩胺醯胺,其衍生物與其用途,及其製法 - Google Patents
標記〔f-18〕之l-麩胺酸,標記〔f-18〕之l-麩胺醯胺,其衍生物與其用途,及其製法 Download PDFInfo
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- TWI415626B TWI415626B TW096141249A TW96141249A TWI415626B TW I415626 B TWI415626 B TW I415626B TW 096141249 A TW096141249 A TW 096141249A TW 96141249 A TW96141249 A TW 96141249A TW I415626 B TWI415626 B TW I415626B
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- 238000002360 preparation method Methods 0.000 title claims description 12
- 229960002989 glutamic acid Drugs 0.000 title abstract description 30
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 title abstract description 18
- QMYMCAZUEQJSED-HVDRVSQOSA-N N1C=CC2=CC=CC=C12.N[C@@H](CCC(N)=O)C(=O)O Chemical compound N1C=CC2=CC=CC=C12.N[C@@H](CCC(N)=O)C(=O)O QMYMCAZUEQJSED-HVDRVSQOSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 217
- -1 ethoxy, methoxy Chemical group 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 206010028980 Neoplasm Diseases 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
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- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 13
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
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- 238000003745 diagnosis Methods 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 8
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 34
- 238000003786 synthesis reaction Methods 0.000 abstract description 32
- 229930195714 L-glutamate Natural products 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 127
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000002904 solvent Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
- 238000004128 high performance liquid chromatography Methods 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 230000002285 radioactive effect Effects 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- 238000004809 thin layer chromatography Methods 0.000 description 24
- 239000004220 glutamic acid Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 239000002585 base Substances 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 16
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 16
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- 239000000010 aprotic solvent Substances 0.000 description 13
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 13
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
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- AOYNUTHNTBLRMT-SLPGGIOYSA-N 2-deoxy-2-fluoro-aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](F)C=O AOYNUTHNTBLRMT-SLPGGIOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
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- FFNSNPPPOXRILG-UHFFFAOYSA-N dimethyl 2-[1-bromo-6-[(2-methylpropan-2-yl)oxycarbonylamino]heptan-4-yl]propanedioate Chemical compound COC(=O)C(C(=O)OC)C(CCCBr)CC(C)NC(=O)OC(C)(C)C FFNSNPPPOXRILG-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000012636 positron electron tomography Methods 0.000 description 10
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- 201000011510 cancer Diseases 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- WCNGSWZQXODHHH-UHFFFAOYSA-N dimethyl 2-[3-[2-(4-methylphenyl)sulfonyloxyethoxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]propanedioate Chemical compound CC(C)(C)OC(=O)NC(C(C(=O)OC)C(=O)OC)CC(C)OCCOS(=O)(=O)C1=CC=C(C)C=C1 WCNGSWZQXODHHH-UHFFFAOYSA-N 0.000 description 7
- NHMIUKKQQRHSKJ-UHFFFAOYSA-N dimethyl 2-[3-methyl-7-(4-methylphenyl)sulfonyloxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]heptyl]propanedioate Chemical compound CC(C)(C)OC(=O)NC(C(C(=O)OC)C(=O)OC)CC(C)CCCCOS(=O)(=O)C1=CC=C(C)C=C1 NHMIUKKQQRHSKJ-UHFFFAOYSA-N 0.000 description 7
- FKTNWNRHXWXIKA-UHFFFAOYSA-N dimethyl 2-[6-fluoro-3-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]propanedioate Chemical compound CC(C)(C)OC(=O)NC(C(C(=O)OC)C(=O)OC)CC(C)CCCF FKTNWNRHXWXIKA-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
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- C07C309/66—Methanesulfonates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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RU2006138584/04A RU2395489C2 (ru) | 2006-11-01 | 2006-11-01 | [f-18] меченная l-глютаминовая кислота, [f-18] меченный l-глютамин, их производные и их применение, а также способ их получения |
EP06090211A EP1923382A1 (de) | 2006-11-18 | 2006-11-18 | [F-18] markierte L-Glutaminsäure, [F-18] markiertes Glutamin, ihre Derivate und ihre Verwendung sowie Verfahren zu ihrer Herstellung |
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CL (2) | CL2007003169A1 (no) |
CO (1) | CO6180453A2 (no) |
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EC (1) | ECSP099304A (no) |
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IL (1) | IL198022A0 (no) |
MX (1) | MX2009004686A (no) |
NO (1) | NO20092123L (no) |
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PE (1) | PE20091723A1 (no) |
SV (1) | SV2009003251A (no) |
TW (1) | TWI415626B (no) |
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Families Citing this family (20)
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EP2123621A1 (de) * | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
CA2667395C (en) * | 2006-11-01 | 2016-05-10 | Bayer Schering Pharma Aktiengesellschaft | [f-18]-labeled l-glutamic acid, [f-18]-labeled l-glutamine, their derivatives and their use and processes for their preparation |
EP2123619A1 (de) * | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma AG | Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
EP2123620A1 (en) * | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | {F-19}-labeled L-Glutamic acid and L-Glutamine derivative (III), use thereof and method for obtaining them |
US20110286921A1 (en) * | 2008-10-10 | 2011-11-24 | Merck & Cie | 18f-labelled folates as pet radiotracers |
US8722014B2 (en) * | 2009-05-01 | 2014-05-13 | Washington University | 1 H-[1, 2, 3] triazole substituted amino acids and uses thereof |
US8747809B2 (en) | 2009-08-14 | 2014-06-10 | The Trustees Of The University Of Pennsylvania | Single diastereomers of 4-fluoroglutamine and methods of their preparation and use |
CA2780840A1 (en) * | 2009-11-17 | 2011-05-26 | Bayer Pharma Aktiengesellschaft | Iodine-labeled homoglutamic acid and glutamic acid derivatives |
KR20120101452A (ko) * | 2009-11-17 | 2012-09-13 | 바이엘 파마 악티엔게젤샤프트 | F-18 표지된 글루탐산 유도체의 제조 방법 |
EP2322171A3 (en) * | 2009-11-17 | 2011-06-01 | Bayer Schering Pharma Aktiengesellschaft | Fluorine labeled L-glutamic acid derivatives |
EP2338892A1 (en) * | 2009-12-18 | 2011-06-29 | Bayer Schering Pharma Aktiengesellschaft | Prostate specific membrane antigen inhibitors |
WO2012092394A1 (en) | 2010-12-29 | 2012-07-05 | Cardinal Health 414, Llc | Closed vial fill system for aseptic dispensing |
EP2520557A1 (en) | 2011-05-03 | 2012-11-07 | Bayer Pharma Aktiengesellschaft | Novel precursors of glutamate derivatives |
EP2520556A1 (en) | 2011-05-03 | 2012-11-07 | Bayer Pharma Aktiengesellschaft | Radiolabeled amino acids for diagnostic imaging |
US9417332B2 (en) | 2011-07-15 | 2016-08-16 | Cardinal Health 414, Llc | Radiopharmaceutical CZT sensor and apparatus |
US20130102772A1 (en) | 2011-07-15 | 2013-04-25 | Cardinal Health 414, Llc | Systems, methods and devices for producing, manufacturing and control of radiopharmaceuticals-full |
US20130022525A1 (en) * | 2011-07-15 | 2013-01-24 | Cardinal Health 414, Llc | Methods and compositions for drying in the preparation of radiopharmaceuticals |
WO2013012813A1 (en) | 2011-07-15 | 2013-01-24 | Cardinal Health 414, Llc | Modular cassette synthesis unit |
WO2020010228A1 (en) * | 2018-07-06 | 2020-01-09 | The Regents Of The University Of California | Deconstructive functionalization methods and compounds |
CN109369445B (zh) * | 2018-11-20 | 2021-10-15 | 首都医科大学 | 用于诊断和治疗的放射性谷氨酰胺衍生物及其制备方法 |
Citations (3)
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US20050240098A1 (en) * | 2004-04-15 | 2005-10-27 | Sheng-Ping Zhong | Magnetic resonance imaging of a medical device and proximate body tissue |
US20060127306A1 (en) * | 2002-08-02 | 2006-06-15 | Mertens John J | Radioactively labelled amino acid analogues, their preparation and use |
WO2007008287A2 (en) * | 2005-07-07 | 2007-01-18 | Alderman Joseph B | Attaching and managing a real estate covenant |
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FR1461184A (fr) * | 1964-12-23 | 1966-01-07 | Takeda Chemical Industries Ltd | Procédé de préparation d'isoxazolidones substituées en position 5 |
DE1620522A1 (de) * | 1964-12-23 | 1970-04-23 | Takeda Chemical Industries Ltd | Verfahren zur Herstellung von 5-substituierten Isoxazolidonverbindungen |
US5264570A (en) * | 1992-08-05 | 1993-11-23 | General Electric Company | Method for making 2-[18 F]fluoro-2-deoxy-D-glucose |
US5267570A (en) * | 1992-12-30 | 1993-12-07 | Preston Myra S | Method of diagnosing and treating chronic fatigue syndrome |
GB9324872D0 (en) | 1993-12-03 | 1994-01-19 | Univ Pasteur | Pharmaceutical compounds |
US6506799B1 (en) * | 1999-04-01 | 2003-01-14 | Esperion Therapeutics, Inc. | Methods of treating cardiovascular diseases, dyslipidemia, dyslipoproteinemia, and hypertension with ether compounds |
AU2001278945A1 (en) | 2000-08-10 | 2002-02-25 | Eli Lilly And Company | 4-substituted d-glutamic acid derivatives for use as antibiotic |
WO2002018941A2 (en) | 2000-09-01 | 2002-03-07 | Annovis, Inc. | Screen for glutamate reuptake inhibitors, stimulators, and modulators |
DE10223451A1 (de) * | 2002-05-25 | 2003-12-24 | Abx Gmbh | Verfahren zur Herstellung von 18F-fluorierten alpha-Aminosäuren |
DE10346228B4 (de) * | 2003-09-25 | 2009-04-09 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Herstellung von [18F]fluormarkierten aromatischen L-Aminosäuren |
US7270799B2 (en) * | 2004-01-15 | 2007-09-18 | Nst Neurosurvival Technologies Ltd. | Perturbed membrane-binding compounds and methods of using the same |
EP1923382A1 (de) | 2006-11-18 | 2008-05-21 | Bayer Schering Pharma Aktiengesellschaft | [F-18] markierte L-Glutaminsäure, [F-18] markiertes Glutamin, ihre Derivate und ihre Verwendung sowie Verfahren zu ihrer Herstellung |
CA2667395C (en) | 2006-11-01 | 2016-05-10 | Bayer Schering Pharma Aktiengesellschaft | [f-18]-labeled l-glutamic acid, [f-18]-labeled l-glutamine, their derivatives and their use and processes for their preparation |
EP2123621A1 (de) | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
EP2123620A1 (en) * | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | {F-19}-labeled L-Glutamic acid and L-Glutamine derivative (III), use thereof and method for obtaining them |
EP2123619A1 (de) * | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma AG | Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
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2007
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2008
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2009
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2010
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2012
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2013
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2014
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